4-Methyl-2-oxovaleric acid → HCID 178446426, compound

HRID 2418432Notes

Reaction equation

[CH3:1][CH:2]([CH3:9])[CH2:3][C:4](=O)[C:5]([OH:7])=[O:6].[NH2:10][C@H:11]([C:18]([NH:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1.C([BH3-])#N.[Na+]>>[C:5]([CH:4]([NH:10][C@H:11]([C:18]([NH:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][CH:23]([CH3:24])[CH3:25])=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)[CH2:3][CH:2]([CH3:9])[CH3:1])([OH:7])=[O:6]

Participants

Reactant 3

HCID 704-Methyl-2-oxovaleric acid

HCID 5003444Sodium cyanoborohydride

HCID 178446018HCID 178446018, compound

Product 1

HCID 178446426HCID 178446426, compound

Procedure

In the manner described in Example 54, 4-methyl-2-oxopentanoic acid and L-histidyl-L-leucine are condensed in the presence of sodium cyanoborohydride to yield N-(1-carboxy-3-methylbutyl)-L-histidyl-L-leucine. In this case the product is eluted from the ion exchange resin with 10% ammonia. The mass spectrum shows a molecular ion at 408 m/e for the disilylated species minus 18. The nmr spectrum is consistent with structure.

Sources & evidence

ORD record: ord-d4a25249a23e4107b814d8dd7f35d376
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472380

Reaction notes

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